Potassium Carbonate → Pirfenidone

HRID 1191689Notes

Reaction equation

HRID 1191689 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Cu]>[CH3:8][C:5]1[CH:6]=[CH:7][C:2](=[O:1])[N:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 178426911HCID 178426911, compound

Product 1

HCID 40632PirfenidoneYield 56%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
185 °C

Procedure

A finely pulverized mixture of 2-hydroxy-5-methylpyridine (0.500 g, 4.58 mmol), anhydrous potassium carbonate (0.693 g, 6.41 mmol), copper powder (0.006 g, 0.09 mmol) and iodobenzene (1.68 g, 8.26 mmol) was heated at 180-190° C. for 7 hours. The mixture was cooled, and standard extractive workup was performed to afford a brown residue which was triturated with petroleum ether and recrystallized from hot water to yield the title compound as a white solid (0.470 g, 56%). m.p. 105-107° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.50 (s, 3H), 6.43 (d, J=9.3 Hz, 1H), 7.36-7.53 (m, 7H); IR (KBr) υ 3045, 1675, 1611, 1531, 1270 cm−1; MS 186 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. customto afford a brown residue which
  3. customwas triturated with petroleum ether
  4. customrecrystallized from hot water

Sources & evidence

ORD record
ord-6f87aa49b1dc4094985bec1ef10ec65a
Source dataset
uspto-grants-2014_03
Patent number
US08680123B1

Reaction notes

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